The Cubs are back on the playoff track for a second straight season, which would be routine for a big-market club if it had actually been routine over the last five years. Instead, Chicago enters October with a familiar mix of confidence and doubt, a team good enough to get here but still carrying real questions about how far this run can go.
That tension hangs over everything. The Cubs have a clear path to making noise in the National League Wild Card round, but the playoff picture has been complicated by the Alex Bregman injury and by uncertainty in the bullpen.
Craig Counsell deserves a big share of the credit for getting them this far. There’s a real argument that he belongs in the NL Manager of the Year conversation, even if Pat Murphy’s work with the Milwaukee Brewers may have already become too familiar to voters and Walt Weiss of the Atlanta Braves and Don Mattingly of the Philadelphia Phillies could end up ahead of him.
Counsell has plenty of critics, most of them fixated on his salary, but that hasn’t changed the reality of his season. His pitching staff has been battered for most of the year, and he’s gone much of the last two seasons without a true ace.
The Cubs still found their way into the postseason.
Pete Crow-Armstrong has been the other major force behind the push. Chicago rolled the dice early by signing him to a pre-arbitration contract extension, betting that last season’s second-half struggles were more of a detour than a trend.
The bet paid off in a huge way. Crow-Armstrong has put together a historic season and is on his way to the NL MVP Award.
Strip him out of the picture, and the Cubs are not a playoff team.
David Peterson has also been a major stabilizer since joining the club this season. In 15 appearances, he has allowed two runs or fewer in 11 of them, and even with the occasional rough outing, he has given the rotation a steadier feel. At this point, the best move for Chicago in the NL Wild Card series might be to hand Peterson the ball in a potential Game 3.
Not every part of the roster has been as encouraging. Jed Hoyer’s overall body of work heading into this season and at the trade deadline was solid.
Alex Bregman looks like one of the best signings from last offseason, and the Cubs did act aggressively when the deadline arrived. But the bullpen remains the most obvious danger, and Hoyer takes a hit for missing on Phil Maton and Hunter Harvey.
That’s especially costly now that the relief group is the biggest concern facing the team.
Jacob Webb belongs in that same uneasy category. He allowed six runs on six hits, including two home runs, over his last five innings of work. His strong stretch in the middle of the season helped get the Cubs to this point, but since August 22 he has made a case that he should not be trusted in high-leverage spots.
In Other News...
Cubs Could Turn To An Unexpected Playoff X-Factor Or Two
The Cubs are weighing a few less obvious names as they shape their playoff roster for the National League Division Series, a reminder that October often rewards flexibility as much as star power. Justin Steele has given the club a reason to think about left-handed help after showing promise in a rehab outing, while Justin Dean offers a different kind of value as a speed-first outfielder who has mostly filled a pinch-running role.
Gavin Hollowell is also in the conversation after working back from a shoulder injury and turning in strong rehab appearances. None of these choices is set in stone, but the possibility of carrying an extra arm or a specialist runner speaks to how the Cubs are trying to cover specific postseason needs, even if the final decisions are still to come. [Read more 🡒]
Cubs Fans May Need To Watch Carter Hawkins This Offseason
The Red Sox spent the day locking in their baseball leadership, with manager Chad Tracy getting a three-year contract extension after stepping in on an interim basis in April and executive Craig Breslow having club options exercised for the 2029 and 2030 seasons. It was a clear sign Boston wants continuity at the top, and it also quietly sharpened the broader front-office market for anyone around the league keeping an eye on possible movement.
For Cubs fans, the ripple effect could be worth watching. Chicago executive Carter Hawkins is already being mentioned as the kind of name that can surface when front office openings start to appear, and this kind of shuffle only adds to the possibility that his offseason could become more interesting than expected. If the Red Sox are settling in, other clubs may soon be looking for the same sort of stability, and that is where Hawkins starts to enter the conversation. [Read more 🡒]
Cubs Suddenly Face A Bigger Edward Cabrera Problem Than October
Edward Cabrera arrived as the kind of rotation upgrade the Cubs hoped would steady things down the stretch, but the blister issues that pushed him into the bullpen have only complicated the picture. Chicago made the move to try to keep him effective and available, yet the role change has not produced the immediate lift the club wanted from a pitcher it believed could help as a top starter.
Now the bigger question is not just how Cabrera fits into October plans, but whether he can even pitch his way onto the playoff roster in a meaningful way. A rough outing that saw him give up three runs in less than an inning only sharpened the concern, and with his numbers trending the wrong direction this season, the Cubs may be heading toward a longer offseason evaluation of what Cabrera is at this point and what he can still become. [Read more 🡒]